- On the reaction of 1,3-dichloro-2-azoniaallene salts with olefins and diphenylacetylene
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1,3-Diaryl-1,3-dichloro-2-azoniaallene salts 1 react with di-, tri- and tetraalkyl and aryl substituted olefins to form new types of 2-azoniaallene salts 4, a 4-azapentadienyl salt 5e or pyridinium salts 8, respectively. The cycloaddition of olefins to 1,
- Hitzler,Freyhardt,Jochims
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- TMSOTf-mediated Kr?hnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
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An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid additive to Sn(OTf)2, and the desired product was also confirmed using X-ray single-crystal diffraction analysis.
- Chan, Chieh-Kai,Chung, Yi-Hsiu,Wang, Cheng-Chung
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p. 8263 - 8273
(2022/04/07)
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- Synthesis of Kr?hnke pyridines through iron-catalyzed oxidative condensation/double alkynylation/amination cascade strategy
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An efficient protocol for the synthesis of symmetrical and unsymmetrical 2,4,6-trisubstituted pyridines via oxidative cascade annulation of arylacetylenes with benzylamines has been developed. The reaction proceeds smoothly utilizing iron(II) triflate as a catalyst and molecular oxygen as an oxidant with broad substrate scope. Mechanistic studies reveal that the reaction may be experiences an oxidative condensation followed by double alkynylation and amination process.
- Gopalaiah, Kovuru,Choudhary, Renu
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supporting information
(2021/09/15)
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- Copper-catalyzed efficient access to 2,4,6-triphenyl pyridinesviaoxidative decarboxylative coupling of aryl acetic acids with oxime acetates
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An efficient and concise approach for the synthesis of 2,4,6-triphenyl pyridines has been developed through copper-catalysed oxidative decarboxylative coupling of C(sp3) aryl acetic acids with oxime acetates in DMF at 150 °C under an oxygen atm
- Bharat Kumar, Karasala,Chinnari, Lekkala,Shyamala, Pulipaka,Siddaiah, Vidavalur,Varaprasad, Bodala
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supporting information
p. 15205 - 15209
(2021/09/06)
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- Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives
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In this study, three eco-friendly, efficient, and convenient protocols have been reported for one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, the easy isolation of products by filtering, short reaction times, simple methodology, and good yields.
- Roozifar, Majid,Hazeri, Nourallah,Faroughi Niya, Homayoun
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p. 1117 - 1129
(2021/02/26)
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- Synthesis of triphenylpyridines: Via an oxidative cyclization reaction using Sr-doped LaCoO3 perovskite as a recyclable heterogeneous catalyst
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An La0.6Sr0.4CoO3 strontium-doped lanthanum cobaltite perovskite was prepared via a gelation and calcination approach and used as a heterogeneous catalyst for the synthesis of triphenylpyridines via the cyclization reactio
- Le, Thu N. M.,Doan, Son H.,Pham, Phuc H.,Trinh, Khang H.,Huynh, Tien V.,Tran, Tien T. T.,Le, Minh-Vien,Nguyen, Tung T.,Phan, Nam T. S.
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p. 23876 - 23887
(2019/08/12)
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- A Facile and Green Synthesis of 2,4,6-Triarylpyridine Derivatives Using the Modified Mesoporous Organic Polymer Based on Calix [4]Resorcinarene: As an Efficient and Reusable Heterogeneous Acidic Catalyst
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Abstract: The work describes an efficient one-pot synthesis of 2,4,6-trisubstituted pyridine derivatives through a three-component catalytic reaction. The procedure involves mesoporous organic polymer based on calix[4]resorcinarene in and functionalized b
- Mouradzadegun,Mostafavi,Ganjali
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p. 187 - 195
(2019/05/27)
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- A New Synthetic Pathway to Triphenylpyridines via Cascade Reactions Utilizing a New Iron-Organic Framework as a Recyclable Heterogeneous Catalyst
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A new iron-organic framework, VNU-22 {[Fe3(BTC)(BPDC)2]·11.97H2O}, constructed from BTC3–, BPDC2– pillars and infinite [Fe3(CO2)7]∞ rod SBU, was obtained. The VNU-22 was utilized as a heterogeneous catalyst in the synthesis of 2,4,6-triphenylpyridines via cascade reactions from acetophenones and phenylacetic acids with ammonium acetate as a nitrogen source. This transformation is new. The VNU-22 was more active in the cascade reactions than many homogeneous and heterogeneous catalysts. The framework catalyst was recovered and reutilized without an appreciable decline in its performance. To our best knowledge, this synthetic pathway to 2,4,6-triphenylpyridines was not previously reported, and would attract interests from the chemical industry.
- Doan, Son H.,Tran, Nhu K. Q.,Pham, Phuc H.,Nguyen, Vu H. H.,Nguyen, Ngoc N.,Ha, Phuong T. M.,Li, Shuang,Le, Ha V.,Le, Nhan T. H.,Tu, Thach N.,Phan, Nam T. S.
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supporting information
p. 2382 - 2389
(2019/03/27)
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- A new route to triphenylpyridines utilizing ketoximes as building blocks via cascade reactions under iron-organic framework catalysis
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Iron-based metal–organic framework VNU-20 was utilized as a heterogeneous catalyst for cascade reactions between ketoximes and dibenzyl ether to produce 2,4,6-triphenylpyridines. Additionally, benzyl alcohol and (dimethoxymethyl)benzene could be used as an alternative starting materials for the transformation. The oxidant exhibited a remarkable impact on the reactions, and di-tert-butylperoxide was the most appropriate candidate. The VNU-20 displayed higher efficiency than many homogeneous and heterogeneous catalysts. The catalyst was reusable for the cascade reactions without a noticeable deterioration in catalytic activity. This transformation is new, and would offer alternative routes to triphenylpyridines utilizing ketoximes as building blocks.
- Nguyen, Vu H.H.,Doan, Son H.,Van, Tram T.,Pham, Phuc H.,Nguyen, Tran T.N.,Nguyen, Ngoc N.,Tu, Thach N.,Phan, Nam T.S.
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- Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines
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Metal-free, base-free, biomimetic and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed under mild conditions for the first time. The heterogeneous biomimetic catalyst-recoverable Merrifield resin-supported quinone-was fully characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectrometry (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported quinone catalyst exhibited excellent catalytic reactivity for chemoselective synthesis of 2,4,6-trisubstituted pyridines, providing an efficient and green method for the synthesis of pyridine derivatives under mild conditions. Mechanistic investigations were conducted to gain insights into the heterogeneous biomimetic catalyst as well as the resulting transformation. The successful capture of intermediates offered direct and clear evidence for the proposed mechanism.
- Yang, Qing,Zhang, Yilin,Zeng, Wei,Duan, Zheng-Chao,Sang, Xinxin,Wang, Dawei
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supporting information
p. 5683 - 5690
(2019/10/22)
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- An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions
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A simple and efficient protocol developed for one pot three-component synthesis of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate using the versatile super Br?nsted acid triflimide (HNTf2) as an effective catalyst is described. The reactions proceed well in the presence of 1 mol% of HNTf2 at 80 °c under solvent-free conditions and provide the corresponding triarylpyridines in good to excellent yields. The method reported has several advantages such as a metal-free and commercially available catalyst, mild reaction conditions and lower loading of catalyst.
- Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
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p. 5158 - 5163
(2019/02/27)
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- Transition-metal-free selective pyrimidines and pyridines formation from aromatic ketones, aldehydes and ammonium salts
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An efficient synthesis of pyrimidines and pyridines has been developed from readily available aromatic ketones, aldehydes and ammonium salts under transition-metal-free conditions. In this strategy, ammonium salts were used as nitrogen sources and only wa
- Chen, Jinjin,Meng, Huanxin,Zhang, Feng,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 5201 - 5206
(2019/10/11)
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- Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf?-catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water
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The cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf? is easy to prepare and stable in air. The catalytic activity of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? as a neutral organotin Lewis acid catalyst is probed through the one-pot three-component syntheses of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1?mol% of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? in water and provide the corresponding 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.
- Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
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- Application of a novel, efficient and recyclable photo redox catalyst (Zn–Al layered double hydroxide/eosin) for the synthesis of substituted pyridine derivatives under visible light irradiation
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Layered double hydroxides (LDHs) are a class of anionic clays with brucite-like layers and interlayer anions and varying in composition and morphology. LDHs show potential as supports for the immobilization of catalytically active species, to synthesize recyclable catalysts, in which catalytic sites can be preferentially orientated, highly dispersed and stabilized to afford high catalytic efficiency and recyclability in reaction media. Redox active organic dyes such as eosin Y with strong absorption in the visible region of the spectrum have been successfully used. In this work, an intercalated photo redox catalyst (Zn–Al LDH/eosin) was synthesized by co-precipitation of an aqueous solution of zinc nitrate and aluminium nitrate simultaneously with eosin Y as anionic dye. Zn–Al LDH/eosin as a recyclable catalyst was used in the reaction of various aryl ketones and benzylamines under molecular oxygen and visible light, giving good yields of substituted pyridines at room temperature. Also, the Zn–Al LDH/eosin catalyst could be reused three times without any significant changes in the reaction yields.
- Rasouli, Nahid
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- B(C6F5)3-catalyzed oxidative deamination/cyclization cascade reaction of benzylamines and ketones for the synthesis of 2,4,6-triarylpyridines
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The B(C6F5)3-catalyzed oxidative deamination/cyclization cascade reaction of benzylamines and ketones for the construction of 2,4,6-triarylpyridines under metal-/solvent-free conditions has been successfully achieved. The advantages of this strategy include good functional group tolerance, low catalyst loading and high yields.
- Ling, Fei,Shen, Leixin,Pan, Zhentao,Fang, Lu,Song, Dingguo,Xie, Zhen,Zhong, Weihui
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supporting information
p. 3678 - 3682
(2018/09/11)
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- An efficient, green solvent-free protocol for the synthesis of 2,4,6-triarylpyridines using reusable heterogeneous activated Fuller’s earth catalyst
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Abstract: A simple, efficient, and green method of preparation for the synthesis of highly substituted pyridines by multicomponent reaction of acetophenones, aldehydes, and ammonium acetate using activated Fuller’s earth as an effective and reusable heterogeneous catalyst is described. The advantages of the present protocol include simple procedure with an easy workup procedure, mild reaction conditions, and high yields of the products. The performance of this reaction under solvent-free conditions using heterogeneous catalysts, such as activated Fuller’s earth, could enhance its efficiency from an economic as well as ecological point of view. Graphical abstract: [Figure not available: see fulltext.].
- Rekunge, Deelip S.,Kale, Ishwari A.,Chaturbhuj, Ganesh U.
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p. 2455 - 2462
(2018/09/13)
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- Synthesis and application of chitosan supported vanadium oxo in the synthesis of 1,4-dihydropyridines and 2,4,6-triarylpyridines: Via anomeric based oxidation
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Chitosan, as a biopolymer, exhibits a strong affinity for complexation with suitable metal ions. Thus, it has received increased attention for the preparation of stable bioorganic-inorganic hybrid heterogeneous catalysts. Herein, a novel chitosan based vanadium oxo (ChVO) catalyst was prepared and fully characterized by several techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), derivative thermal gravimetric (DTG), differential thermal analysis (DTA), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), high-resolution transmission electron microscopy (HRTEM), selected area electron diffraction (SAED), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma mass spectrometry (ICP-MS). The synthesized catalyst has been successfully used as a reusable catalyst in the synthesis of dihydropyridines and triarylpyridines.
- Safaiee, Maliheh,Ebrahimghasri, Bahar,Zolfigol, Mohammad Ali,Baghery, Saeed,Khoshnood, Abbas,Alonso, Diego A.
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p. 12539 - 12548
(2018/08/04)
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- Direct C-H Functionalization of Pyridine via a Transient Activator Strategy: Synthesis of 2,6-Diarylpyridines
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A Pd-catalyzed highly selective direct diarylation of pyridines has been developed using a transient activator strategy. Both (MeO)2SO2 and Cu2O are required for this transformation. The in situ generated N-methylpyridinium salt can be arylated at both 2- and 6-positions under the cooperative Pd/Cu catalysis. A subsequent N-demethylation then gives the 2,6-diarylpyridines. This protocol provides a novel synthetic route for the symmetric 2,6-diarylpyridines.
- Zeng, Yang,Zhang, Chunchun,Yin, Changzhen,Sun, Maoshen,Fu, Haiyan,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Chen, Hua
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supporting information
p. 1970 - 1973
(2017/04/27)
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- Method for double carbon-hydrogen activation and arylation of pyridine compounds
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The invention discloses a method for double carbon-hydrogen activation and arylation of pyridine compounds, and belongs to the field of methodology of organic synthesis. The method comprises the following steps: mixing a palladium source, a phosphine ligand, a copper salt or an oxide of copper, an alkali and aryl halide, placing the mixture in a nitrogen gas environment, then adding an additive, 4-substituted pyridine and a solvent, and carrying out a heating reaction, to obtain a C2-site and C6-site double aryl substituted pyridine compounds through a carbon-hydrogen activation mechanism, wherein a substituent group of 4-substituted pyridine is any one of hydrogen, alkyl and aryl. The method has the advantages of wide application range, simple operation steps, no need of pre-activation of a pyridine ring, and no need of introduction of a guiding group, and extremely high atomic economy and practicability.
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Paragraph 0062; 0063; 0064; 0065; 0066; 0079; 0080; 0081-008
(2017/04/21)
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- Synthesis of tri-substituted pyridine derivatives
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The invention provides a method for compounding tri-substituted pyridine derivatives, which belongs to the compound technical field of pyridine derivatives. The method for compounding the tri-substituted pyridine derivatives use amine compounds and troponoid compounds to react and compound pyridine derivatives when having trifluoromethanesulfonic acids, wherein a response equation is (img file='878185 dest_path_image001.TIF' wi='250' he='66'/). The method for compounding the tri-substituted pyridine derivatives is suitable for a large number of functional groups, and is simple in operation and high in yield, single in product structure, convenient to separate and purify, safe, low in price and small in pollution.
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Paragraph 0048
(2017/09/26)
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- Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines via Iodine-Initiated Reaction of Methyl Aryl Ketones with Amines under Neat Heating
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A neat heating protocol has been developed for metal-free synthesis of various 2,4,6-trisubstituted pyridines via iodine-initiated (in situ generated HI-catalyzed) condensation of methyl aryl ketones with amines and the following cyclization-aerobic oxidation. Large-scale synthesis and mechanistic investigation were also performed.
- Xu, Hui,Zeng, Ji-Chao,Wang, Fang-Jian,Zhang, Ze
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supporting information
p. 1879 - 1883
(2017/04/06)
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- Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes
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A novel and facile iron-catalyzed cyclization of ketoxime acetates and aldehydes for the green synthesis of substituted pyridines has been developed. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce 2,4,6-triarylsubstituted symmetrical pyridines in high yields in the absence of any additive. A gram-scale reaction sequence was performed to demonstrate the scaled-up applicability of this synthetic method.
- Yi, Yukun,Zhao, Mi-Na,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 1023 - 1027
(2017/08/18)
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- An Efficient Synthesis of 2,4,6-Triarylpyridines by Use of Benzyl Halides under Neat Conditions
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An efficient synthesis of 2,4,6-triarylpyridines is described. Heating a mixture of an acetophenone, a benzyl halide, and ammonium acetate under neat conditions afforded the corresponding Kr?hnke pyridines in excellent yields.
- Adib, Mehdi,Ayashi, Neda,Mirzaei, Peiman
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p. 417 - 421
(2016/02/09)
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- HOTf-catalyzed sustainable one-pot synthesis of benzene and pyridine derivatives under solvent-free conditions
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Herein a versatile HOTf-catalyzed and solvent-free system for highly efficient one-pot synthesis of privileged benzene and pyridine derivatives has been developed using ketones and ketones with amines as simple substrates, respectively. The remarkable features of this "green" reaction include good to excellent yields, exclusive chemoselectivity and broad substrate/functional group tolerance.
- Zhang, Xu,Wang, Zhiqiang,Xu, Kun,Feng, Yuquan,Zhao, Wei,Xu, Xuefeng,Yan, Yanlei,Yi, Wei
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supporting information
p. 2313 - 2316
(2016/05/19)
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- Copper(II) supported on magnetic chitosan: A green nanocatalyst for the synthesis of 2,4,6-triaryl pyridines by C-N bond cleavage of benzylamines
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In this paper, Cu/magnetic chitosan has been synthesized and used as a new green nanocatalyst for highly efficient synthesis of 2,4,6-triaryl pyridines via C-N bond cleavage of benzylamines under aerobic oxidation at 90 °C. The chemical and structural properties of the synthesized catalyst were determined by scanning electron microscopy, energy-dispersive X-ray, X-ray powder diffraction, thermogravimetric analysis and flame atomic absorption spectroscopies. It is found that the catalyst can be easily separated from the reaction mixture by an external magnetic field and recycled several times without a significant loss in activity.
- Shaabani, Ahmad,Borjian Boroujeni, Mahmoud,Laeini, Mohmmad Sadegh
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p. 27706 - 27713
(2016/03/30)
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- Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin y Photoredox Catalysis
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Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52-87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.
- Rohokale, Rajendra S.,Koenig, Burkhard,Dhavale, Dilip D.
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p. 7121 - 7126
(2016/08/30)
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- Microwave assisted one-pot pseudo four-component synthesis of 2,4,6-trisubstituted pyridines using γ-MnO2 nanoparticles
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This work described an efficient, one-pot pseudo four-component synthesis of 2,4,6-triarylpyridines. This reaction was performed under microwave irradiation and solvent-free conditions in the presence of γ-MnO2 nanoparticles. Herein 2,4,6-triarylpyridines were synthesized via a simple reaction between benzyl alcohols, acetophenone, and ammonium acetate in the presence of γ-MnO2 nanoparticles in good to excellent yields. Eco friendly, excellent yields of the product, short reaction times, inexpensive and readily available starting material are the main advantages of this method. Graphical abstract: [Figure not available: see fulltext.]
- Mohammadi, Bagher
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p. 1939 - 1943
(2016/10/21)
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- Magnetic MIL-101-SO3H: A highly efficient bifunctional nanocatalyst for the synthesis of 1,3,5-triarylbenzenes and 2,4,6-triaryl pyridines
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A magnetic MIL-101-SO3H was synthesized and successfully used as a highly active nanocatalyst for the synthesis of 1,3,5-triarylbenzenes and 2,4,6-triaryl pyridines. The prepared nanocatalyst was characterized by Fourier transform infrared spec
- Boroujeni, Mahmoud Borjian,Hashemzadeh, Alireza,Faroughi, Mohammad-Tayeb,Shaabani, Ahmad,Amini, Mostafa Mohammadpour
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p. 100195 - 100202
(2016/11/09)
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- Ultrasound-Mediated Synthesis of 2,4,6-Triaryl-Pyridines Using MgAl2O4 Nanostructures
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Nanocrystalline MgAl2O4 was found to be a highly efficient catalyst for the preparation of 2,4,6-triaryl-pyridines from the reaction of acetophenone derivatives, aryl aldehydes, and ammonium acetate under sonic condition for the first time. The present methodology offers several advantages, such as excellent yields, simple procedure, shorter reaction times, and milder conditions; the catalyst also exhibited remarkable reusable activity. This procedure is much simpler and faster than the protocols published to date.
- Zarnegar,Safari,Borjian-Borujeni
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p. 1683 - 1691
(2015/02/05)
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- One-pot, solvent-free and efficient synthesis of 2,4,6-triarylpyridines catalyzed by nano-titania-supported sulfonic acid as a novel heterogeneous nanocatalyst
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Nano titania-supported sulfonic acid (n-TSA) has found to be a highly efficient, eco-friendly and recyclable heterogeneous nanocatalyst for the solvent-free synthesis of 2,4,6-triarylpyridines through one-pot three-component reaction of acetophenones, aryl aldehydes and ammonium acetate. This reported method illustrates several advantages such as environmental friendliness reaction conditions, simplicity, short reaction time, easy work up, reusability of catalyst and high yields of the products. One new compound is reported too. Furthermore, the catalyst could be recycled after a simple work-up, and reused at least six times without substantial reduction in its catalytic activity.
- Tabrizian, Elham,Amoozadeh, Ali,Rahmani, Salman,Imanifar, Elham,Azhari, Saeede,Malmir, Masoumeh
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p. 1278 - 1282
(2015/12/31)
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- Nano-Fe3O4-supported, hydrogensulfate ionic liquid-catalyzed, one-pot synthesis of polysubstituted pyridines
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Anchoring 1-methyl-3-(triethoxysilylpropyl) imidazolium chloride onto silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid. Exchanging the Cl- anion by treating with H2SO4 gave Br?nsted ionic liquid 1-methyl-3-(triethoxysilylpropyl) imidazolium hydrogensulfate. The synthesized catalyst was characterized by various techniques such as infrared, x-ray diffraction, scanning electron microscopy, thermogravimetric analysis, and elemental analyses. The results indicated that the prepared catalyst had a nanostructure. The catalytic activity of the supported ionic liquid was examined in the synthesis of the polysubstituted pyridines by reaction of aromatic aldehydes with acetophenones and ammonium acetate in moderate to good yields under solvent-free conditions. The catalyst can be easily recovered by applying an external magnetic field and reused for at least seven runs without deterioration in catalytic activity.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Ghobadi, Neda
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supporting information
p. 1964 - 1976
(2015/08/18)
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- The synthesis of polysubstituted pyridines using nano Fe3O4 supported hydrogensulfate ionic liquid
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Reaction of 1-methylimidazole with 3-(trimethoxysilyl)propyl chloride resulted in formation of 1-methyl-3-(trimethoxysilyl)propyl imidazolium chloride ([pmim]Cl). Anchoring of the ionic liquid on to silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid MNP-[pmim]Cl. Exchanging the Cl- anion by treatment with H2SO4 gave the Bronsted ionic liquid MNP-[pmim]HSO4. FT-IR, XRD, SEM, TEM, TG/DTG, VSM, and CHN analysis were used to characterize the supported ionic liquid. The results indicated the catalyst was a nanostructure. The catalytic activity of the supported ionic liquid was examined in the synthesis of the polysubstituted pyridines by reaction of aromatic aldehydes, and acetophenones or indan-1-one with ammonium acetate under solvent-free conditions. The catalyst could be easily recovered, by applying an external magnetic field, and reused at least six runs without deterioration of its catalytic activity.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Ghobadi, Neda
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p. 9113 - 9127
(2015/10/28)
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- Three-component one-pot synthesis of 2,4,6-triarylpyridines without catalyst and solvent
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An efficient and green synthesis of 2,4,6-triarylpyridines by a one-pot three-component condensation of aromatic aldehydes, substituted acetophenones, and ammonium acetate without catalyst at 130°C under solvent-free conditions is described. This method offers several advantages such as simple procedure, easy work-up, short reaction time, low cost, environmentally friendly conditions, and moderate to high yields.
- Wang, Min,Yang, Zhongyong,Song, Zhiguo,Wang, Qinglin
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p. 907 - 910
(2015/05/13)
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- A facile one-pot synthesis of 2,4,6-triarylpyridine in DMSO
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A facile, efficient and practical method for the one-pot synthesis of 2,4,6-triarylpyridines starting from acetophenones, aryl aldehydes and ammonium acetate by the use of catalytic amounts of 40 % potassium hydroxide in dimethyl sulfoxide is presented. T
- Min, Zhen-Li,Yin, Ting-Zi,Hu, Xia-Min
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p. 7977 - 7980
(2015/02/02)
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- A solvent-free reaction between acetophenone oximes and epoxy styrenes: An efficient synthesis of 2,4,6-triarylpyridines under neutral conditions
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An efficient synthesis of 2,4,6-triarylpyridines is described which involves heating a mixture of an acetophenone oxime and an epoxy styrene under neutral, solvent-free conditions. Kr?hnke pyridine products are obtained in excellent yields.
- Mahernia, Shabnam,Adib, Mehdi,Mahdavi, Mohammad,Nosrati, Meisam
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p. 3844 - 3846
(2014/07/08)
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- Copper-catalyzed formal C-N bond cleavage of aromatic methylamines: Assembly of pyridine derivatives
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An efficient copper-catalyzed C-N bond cleavage of aromatic methylamines was developed to construct pyridine derivatives. With neat conditions and facile operation, the fragment-assembling strategy affords a broad range of 2,4,6-trisubstituted pyridines in up to 95% yield from simple and readily available starting materials. Interestingly, when pyridin-2-yl methylamine was employed as the substrate, α-alkylation reaction of ketones readily occurred to give β-(pyridin-2-yl) ketones instead of the 2,4,6-trisubstituted pyridines.
- Huang, Huawen,Ji, Xiaochen,Wu, Wanqing,Huang, Liangbin,Jiang, Huanfeng
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p. 3774 - 3782
(2013/06/05)
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- Mesoporous nanocrystalline MgAl2O4: A new heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines under solvent-free conditions
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In this paper, one-pot synthesis of 2,4,6-triarylpyridine by condensation of subsisted acetophenone (II), aromatic aldehydes (I), and ammonium acetate (III) in the presence of nanocrystalline MgAl2O4 as a new heterogeneous catalyst under solvent-free conditions is reported. Advantages of this method are the use of spatially-hindered aldehydes such as 2-methoxy-, 2-fluoro-, and 2-chlorobenzaldehydes, a new nanocatalyst with high surface area, shorter reaction time, easier workup, higher yield, and its environmental friendliness. The performance of this reaction under solvent free conditions using heterogeneous catalysts like MgAl2O4 could enhance its efficiency from an economic as well as green chemistry point of view.
- Safari, Javad,Zarnegar, Zohre,Borujeni, Mahmoud Borjian
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p. 688 - 695
(2013/07/26)
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- DPTA-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines
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With diphenylammonium triflate (DPAT) as a catalyst, the highly substituted pyridines and dihydropyridines were prepared under solvent-free conditions from aldehydes, ketones, and amines via a one-pot multi-component reaction. The advantages of this protocol include excellent yields, environmentally benign source of nitrogen, mild reaction conditions, and simple manipulation. Different source of nitrogen like urea, thiourea, inorganic ammonium salts, and organic amines were studied. In addition, a novel way was developed for the conversion of primary aliphatic amines into alcohols.
- Li, Jianjun,He, Ping,Yu, Chuanming
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scheme or table
p. 4138 - 4144
(2012/07/14)
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- Green, new and efficient tandem oxidation and conversion of aryl alcohols to 2,4,6-triarylpyridines promoted by [HMIm]NO3-[BMIm]BF4 as a binary ionic liquid
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A novel, clean and efficient tandem process has been established for the synthesis of 2,4,6-triarylpyridines from primary aryl alcohols or 1-arylethanols using 1-methylimidazolium nitrate in 1-butyl-3-methylimidazolium tetrafluoroborate as a binary task-specific ionic liquid under microwave irradiation.
- Khosropour, Ahmad R.,Mohammadpoor-Baltork, Iraj,Kiani, Forough
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experimental part
p. 441 - 445
(2012/03/22)
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- Copper-Catalyzed coupling of oxime acetates with aldehydes: A new strategy for synthesis of pyridines
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Copper-catalyzed coupling of oxime acetates with aldehydes offers a new strategy for the synthesis of highly substituted pyridines. This novel method tolerates a wide range of functionality and allows for rapid elaboration of the oxime acetates into a variety of substituted pyridines.
- Ren, Zhi-Hui,Zhang, Zhi-Yuan,Yang, Bing-Qin,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 5394 - 5397
(2011/12/02)
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- Barium chloride dispersed on silica gel nanoparticles: An efficient catalyst for the preparation of 2,4,6-triarylpyridines under solvent-free conditions
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BaCl2 dispersed on a nano-structural type of silica gel (BaCl2-nano SiO2) was found to be an effective catalyst for the rapid and high yielding preparation of substituted 2,4,6-triarylpyridine frameworks by the reaction of various aceto-phenones, benzaldehydes and ammonium acetate. The prepared catalyst was characterised by X-ray diffraction and scanning electron microscopy analysis.
- Shafiee, Mohammad Reza Mohammad,Moloudi, Raheleh
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experimental part
p. 294 - 297
(2011/10/05)
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- Solvent-free preparation of 2,4,6-triaryl pyridines using silver(I) nitrate adsorbed on silica gel nanoparticles (AgNO3-Nano SiO2) as an efficient catalyst
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Three-component condensation of substituted acetophenones, aromatic aldehydes, and ammonium acetate catalyzed by silver(I) nitrate adsorbed on silica gel nanoparticles (AgNO3-nano SiO2) has been accomplished for the synthesis of a series of 2,4,6-triaryl pyridines in good to excellent yields under solvent-free conditions.
- Shafiee, Mohammad R.M.,Moloudi, Raheleh
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experimental part
p. 717 - 721
(2012/06/01)
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- PEG-400 catalyzed reaction for the synthesis of 2, 4, 6-Triarylpyridines and crystal structure of 2,4,6-tris(4'-chlorophenyl)pyridine
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An efficient and rapid procedure for synthesizing triarylpyridine compounds under mild reaction conditions has been described. Meanwhile, the crystal structure of 2,4,6-tris(4'-chlorophenyl)pyridine was obtained and determined by X-ray single-crystal diffraction. The procedure is operationally simple, giving good to high product yields.
- He, Qingpeng,Wang, Jianyong,Feng, Ruokun
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experimental part
p. 172 - 177
(2010/08/07)
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- Three-components condensation catalyzed by molecular iodine for the synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin- 2(1H)-ones under solvent-free conditions
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One-pot, three-components synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones was performed under solvent-free conditions using molecular iodine as the catalyst in moderate to good product yields.
- Ren, Yi-Ming,Cai, Chun
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experimental part
p. 49 - 52
(2010/04/06)
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- Microwave-promoted and Lewis acid catalysed synthesis of 2,4,6-triarylpyridines using urea as benign source of ammonia
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An efficient method for the synthesis of 2,4,6-triarylpyridines via microwave-promoted and BF3·OEt2-catalysed one-pot reaction of ω-pyrrolidinoacetophenone with chalcone is reported. This method illustrates urea as an environmentally
- Borthakur, Moyurima,Dutta, Mandakini,Gogoi, Shyamalee,Boruah, Romesh C.
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body text
p. 3125 - 3128
(2009/06/06)
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- A new and convenient one-pot solid supported synthesis of 2,4,6-triarylpyridines
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A new, convenient, efficient and cost-effective one-pot solid supported synthesis of 2,4,6-triarylpyridines from benzylideneacetophenones and urea, thiourea or their derivatives, using Bi(III) nitrate-Al2O3 is described. The reaction seems to proceed via β-oxygenation of Bi(III)-enolized benzylideneacetophenone followed by Michael addition, heteroannulation with simultaneous retro aldol disproportionation and subsequent catalytic oxidation and dehydration.
- Kumar, Anil,Koul, Summon,Razdan, Tej K.,Kapoor, Kamal K.
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p. 837 - 842
(2007/10/03)
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- Synthesis of Some New 2,4,6-Triaryl Substituted Pyridines via Pyridinium Ylides
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Reactions of 4-methoxy phenacyl pyridinium ylide and 4-chlorophenacyl pyridinium ylide with different substituted α-β unsaturated ketones gave a wide variety of 2,4,6-triaryl substituted pyridines which are expected to possess marked biological activities
- Tewari, R. S.,Misra, N. K.
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p. 272 - 273
(2007/10/02)
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- REACTION OF PHENACYLIDENETRIPHENYLARSENANES WITH α,β-UNSATURATED KETONES: SYNTHESIS OF SOME NEW 2,4,6-TRIARYLPYRIDINES
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The reaction of some phenacylidenetriphenylarsenanes with substituted benzylideneacetophenones in the presence of ammonium acetate in acetic acid or methanol gave new 2,4,6-triarylpyridines.Ammonium acetate in acetic acid and ammonium acetate in methanol
- Gupta, K.C.,Srivastava, N.,Nigam, R.K.
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- Studies on Cycloimmonium Ylides. Synthesis of Some 2,4,6-Triaryl-Substituted Pyridines via Isoquinolinium Ylides
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(Aroylmethylene)isoquinolinium ylides on their reaction with different α,β-unsaturated ketones gave a wide variety of 2,4,6-triaryl-substituted pyridines which are expected to possess some potential biological activities.The reaction seemed to proceed via
- Tewari, R. S.,Dubey, A. K.
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